Thieno[3,2-b]pyridine-5(4H)-one derivative compound, preparation method thereof and use thereof

Patent metadata

Field	Value
Publication number	US-11306103-B2
Application number	US-201716768251-A
Country	US
Kind code	B2
Filing date	Dec 27, 2017
Priority date	Nov 30, 2017
Publication date	Apr 19, 2022
Grant date	Apr 19, 2022

Abstract

The present invention relates to a novel thieno[3,2-b]pyridine-5(4H)-one derivative compound, a preparation method thereof, and a use thereof. The novel thieno[3,2-b]pyridine-5(4H)-one derivative compound according to the present invention is synthesized via an aza-[3+3] cyclization addition reaction using BOP, wherein the compound is obtained by synthesizing a 4-arylthiophen-3-amine in which aryl groups such as 4-piperidyl-C6H4, 4-pyrrolidyl-C6H4, 4-MeOC6H4, 3,4,5-(MeO)3C6H4, C6H5, 4-C6H5C6H4, and 4-F3COC6H4 are introduced via a synthesis process by a bromination reaction, a hydrolysis reaction, a decarboxylation reaction, and a Suzuki coupling reaction of methyl 3-aminothiophene carboxylate, and by synthesizing 4-arylthiophen-3-amine and mono-methyl fumarate via a formal aza-[3+3] cyclization addition reaction using BOP and conjugation. Accordingly, novel thieno[3,2-b]pyridine-5(4H)-one derivative compounds according to the present invention have fluorescence properties with a wide range of emission wavelengths and thus may be utilized in various industrial fields such as physics, chemistry, and biomedical research.

First claim

The invention claimed is:

1. A compound selected from the group consisting of the compounds having the structural formulas 3 to 4, and 6 to 28, below:

structure

3

4

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

25

26

27

28

Assignees

• Korea Inst Ocean Sci & Tech

Inventors

• Lee Jong Seok
• Sung Dan Bi
• Mun Bo Hyun
• Lee Hyi Seung
• Lee Yeon Ju
• Lee Ji Hoon
• Shin Hee Jae
• Park Sol

Classifications

• G01N33/533

  with fluorescent label · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• G01N31/221

  for investigating pH value · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title